2-ethoxy-3H-benzo[d][1,2]oxaphosphole 2-oxide | 14707-41-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: 2-ethoxy-3H-benzo[d][1,2]oxaphosphole 2-oxide
• 英文别名: 2-ethoxy-3H-1,2λ5-benzoxaphosphole 2-oxide
• CAS: 14707-41-6
• 化学式: C₉H₁₁O₃P
• 分子量: 198.158
• InChiKey: QLAUKJDVVZODHE-UHFFFAOYSA-N

物化性质

• 熔点：
  60 °C
• 沸点：
  293.3±33.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-ethoxy-3H-benzo[d][1,2]oxaphosphole 2-oxide 在 氯化亚砜 、 水 、 magnesium 、 sodium bromide 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 反应 22.5h， 生成 二苯基(2-羟基苯基甲基)膦氧化物
  参考文献：
  名称：

  Design and synthesis of amphiphilic 2-hydroxybenzylphosphonium salts with antimicrobial and antitumor dual action

  摘要：

  Here we report the synthesis and biological evaluation of a series of new 2-hydroxybenzylphosphonium salts (QPS) with antimicrobial and antitumor dual action. The most active compounds exhibit antimicrobial activity at a micromolar level against Gram-positive bacteria Sa (ATCC 209p and clinical isolates), Bc (1-2 mu M) and fungi Tm and Ca, and induced no notable hemolysis at MIC. The change in nature of substituents of the same length led to a drastic change of biological activity. Self-assembly behavior of the octadecyl and oleyl derivatives was studied. QPS demonstrated self-assembly within the micromolar range with the formation of nanosized aggregates capable of the solubilizing hydrophobic probe. The synthesized phosphonium salts were tested for cytotoxicity. The most potent salt was active against on M - Hela cell line with IC50 on the level of doxorubicin and good selectivity. According to the cytofluorimetry analysis, the salts induced mitochondria-dependent apoptosis.

  DOI：

  10.1016/j.bmcl.2020.127234
• 作为产物：
  描述：

  水杨醇 以 甲苯 为溶剂， 生成 2-ethoxy-3H-benzo[d][1,2]oxaphosphole 2-oxide
  参考文献：
  名称：

  基于取代的 2-羟基苯甲醇的无环和环状膦酸酯的合成

  摘要：

  从水杨醛、水杨酸的衍生物中方便地合成苄基膦酸酯和芳环取代的 2,3-二氢苯并[d][1,2]氧杂磷酰 2-氧化物，以及它们的前体，2-羟基苄醇和 2-羟基苯乙酮在芳环的对位带有一个额外的羟基或甲氧基。首次显示了选择性去甲基化位于亚甲基膦酸酯片段邻位的甲氧基的可能性，而甲氧基保留在对位。

  DOI：

  10.1007/s11172-020-3013-2

文献信息

• 2-Ethoxy-2,3-dihydro[d][1,2]oxaphosphole 2-oxide in the synthesis of dialkyl(diaryl)(2-hydroxybenzyl)phosphine oxides
  作者：D. A. Tatarinov、D. M. Kuznetsov、A. A. Kostin、V. F. Mironov

  DOI：10.1134/s1070363216030063

  日期：2016.3

  A facile method of synthesis of functionally substituted P(IV) derivatives―dialkyl(diaryl)(2-hydroxybenzyl) phosphine oxides―by the reaction of 2-ethoxy-2,3-dihydro[d][1,2]oxaphosphole 2-oxide with organomagnesium compounds, which allows wide variation of substituents on the phosphorus atom was developed.

  通过2-乙氧基-2,3-二氢[ d ] [1,2]恶唑磷2-的反应合成官能取代的P（IV）衍生物-二烷基（二芳基）（2-羟基苄基）氧化膦的简便方法用有机镁化合物制成的氧化物，可以使磷原子上的取代基变化很大。
• Formation of Benzooxaphosphole Oxide Heterocyclic System by the Ring-Contractive Arbuzov-Michaelis Isomerization of Alkoxy-Substituted Benzodioxaphosphorins
  作者：Eduard E. Nifantiev、Svetlana B. Khrebtova、Yulia V. Kulikova、Dmitrii A. Predvoditelv、Tat′yana S. Kukhareva、Pavel V. Petrovskii、Mirjam Rose、Chris Meier

  DOI：10.1080/10426500210234

  日期：2002.1.1

  A possibility of the Arbuzov-Michaelis-type isomerization is revealed for the model 2-ethoxy derivative 4 of the six-membered 4H-benzo[1,3,2]dioxaphosphorin heterocycle. The reaction proceeds with ring contraction to give the five-membered 3H-benzo[d][1,2]oxaphosphole 2-oxide heterocyclic system. Some synthetic possibilities of the new reaction disclosed here are demonstrated by introducing a pharmacophoric 5-O-nucleoside to the P(IV) atom leading to the 3H-benzo[d][1,2]oxaphosphole 2-oxide system by this new rearrangement reaction.
• Synthesis of substituted benzylphosphonic acids
  作者：B. E. Ivanov、L. A. Valitova

  DOI：10.1007/bf01176033

  日期：1967.5
• Influence of Substitution at the Benzylic Position on the Behavior of Stereoisomeric Phosphorus Compounds as Precursors of Stabilized Carbon-Centered Radicals
  作者：Julia Pérez-Prieto、Raquel Eugenia Galian、Pascual Oña Burgos、Maria del Carmen Morant Miñana、Miguel Angel Miranda、Fernando López-Ortiz

  DOI：10.1021/ol051254y

  日期：2005.9.1

  Efficient benzylic radical formation from benzo[d]-1,2-oxaphospholes has demonstrated their suitability as precursors of stabilized C-centered radicals, a property associated with antioxidant potential. A remarkable stereodifferentiation is observed for alkyl- and aryl-substituted derivatives.
• Chasar, Dwight W., Journal of Organic Chemistry, 1983, vol. 48, # 24, p. 4768 - 4769
  作者：Chasar, Dwight W.

  DOI：——

  日期：——